Total Synthesis of Termicalcicolanone A via Organocatalysis and Regioselective Claisen Rearrangement

A total synthesis of an anticancer xanthone natural product termicalcicolanone A utilizing multiple nucleophilic aromatic substitutions and pericyclic reactions has been developed. The pyrano­[3,2-b]­xanthen-6-one scaffold was constructed via NHC-catalyzed aroylation to produce the benzophenone inte...

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Bibliographic Details
Published in:Organic letters 2019-04, Vol.21 (8), p.2777-2781
Main Authors: Ito, Saki, Kitamura, Taiki, Arulmozhiraja, Sundaram, Manabe, Kei, Tokiwa, Hiroaki, Suzuki, Yumiko
Format: Article
Language:English
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Summary:A total synthesis of an anticancer xanthone natural product termicalcicolanone A utilizing multiple nucleophilic aromatic substitutions and pericyclic reactions has been developed. The pyrano­[3,2-b]­xanthen-6-one scaffold was constructed via NHC-catalyzed aroylation to produce the benzophenone intermediate, Claisen cyclization to form the pyran ring, and intramolecular 1,4-addition to construct the xanthone framework. The prenyl group was introduced in the final stages of the synthesis through regioselective Claisen rearrangement. The synthesis has been achieved in 19 steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00731